N^α-Boc 4--L-phenylalanine benzyl ester | 150618-03-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N^α-Boc 4--L-phenylalanine benzyl ester
• 英文别名: benzyl (2S)-3-[4-[diethoxyphosphoryl(difluoro)methyl]phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate
• CAS: 150618-03-4
• 化学式: C₂₆H₃₄F₂NO₇P
• 分子量: 541.529
• InChiKey: WNLYYUCOOVPBAF-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N^α-Boc 4--L-phenylalanine benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到(2S)-2-[(tert-butoxycarbonyl)amino]-3-{4-[(diethoxyphosphoryl)(difluoro)methyl]phenyl}propanoic acid
  参考文献：
  名称：

  制备L-（膦二氟甲基）苯丙氨酸衍生物作为O-磷酸酪氨酸的不可水解模拟物

  摘要：

  Nt-BOC-L-（膦二氟甲基）苯丙氨酸苄酯（1）由Nt-BOC-L-酪氨酸苄基酯O-三氟甲磺酸酯（4）分5步制备。将化合物1进一步转化为可能适合于肽合成的衍生物2和3。类似物1-3是O-磷酸酪氨酸的不可水解模拟物。

  DOI：

  10.1016/s0040-4039(00)73631-8
• 作为产物：
  描述：

  溴氟甲基膦酸二乙酯 在 锌铜偶 、 二氯双(三邻甲苯膦)合钯(II) 、 2,4-滴二甲胺盐 、 copper(I) bromide 、 锌 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 N^α-Boc 4--L-phenylalanine benzyl ester
  参考文献：
  名称：

  Facile syntheses of aryldifluorophosphonate building blocks

  摘要：

  The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used directly in the synthesis of phosphotyrosine analogue F(2)Pmp, and in entering the classical organometallic coupling repertoire via Stille and Suzuki-Miyaura couplings. Herein, we report a streamlined synthesis of F(2)Pmp, and of a pivotal triflate, which undergoes a range of palladium-catalysed couplings with aryl and heteroaryl components. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00266-x

文献信息

• Preparation of L-(Phosphonodifluoromethyl)phenylalanine derivatives as non-hydrolyzable mimetics of O-phosphotyrosine
  作者：Jay Wrobel、Arlene Dietrich

  DOI：10.1016/s0040-4039(00)73631-8

  日期：1993.5

  N-t-BOC-L-(Phosphonodifluoromethyl)phenylalanine benzyl ester (1) was prepared in 5 steps from N-t-BOC-L-tyrosine benzyl eser O-triflate (4). Compound 1 was further converted to derivatives 2 and 3 which are potentially suitable for peptide synthesis. Analogs 1 - 3 are non-hydrolyzable mimetics of O-phosphotyrosine.

  Nt-BOC-L-（膦二氟甲基）苯丙氨酸苄酯（1）由Nt-BOC-L-酪氨酸苄基酯O-三氟甲磺酸酯（4）分5步制备。将化合物1进一步转化为可能适合于肽合成的衍生物2和3。类似物1-3是O-磷酸酪氨酸的不可水解模拟物。
• Small Molecule Degraders of Protein Tyrosine Phosphatase 1B and T‐Cell Protein Tyrosine Phosphatase for Cancer Immunotherapy
  作者：Jiajun Dong、Jinmin Miao、Yiming Miao、Zihan Qu、Sheng Zhang、Peipei Zhu、Florian Wiede、Brenson A. Jassim、Yunpeng Bai、Quyen Nguyen、Jianping Lin、Lan Chen、Tony Tiganis、W. Andy Tao、Zhong-Yin Zhang

  DOI：10.1002/anie.202303818

  日期：——

  An inhibitor for protein tyrosine phosphatase 1B (PTP1B) and T-cell protein tyrosine phosphatase (TC-PTP) was discovered and transformed into a first-in-class, potent, and selective dual PROTAC degrader for both targets. The degrader promotes antigen presentation of tumor cells and activates CD8+ T-cells. Importantly, the degrader is effective in vivo and suppresses syngeneic tumor growth.

  发现了蛋白酪氨酸磷酸酶 1B (PTP1B) 和 T 细胞蛋白酪氨酸磷酸酶 (TC-PTP) 抑制剂，并将其转化为针对这两个靶标的一流、有效、选择性的双 PROTAC 降解剂。该降解剂促进肿瘤细胞的抗原呈递并激活 CD8+ T 细胞。重要的是，该降解剂在体内有效并抑制同基因肿瘤生长。
• Discovery of a selective TC-PTP degrader for cancer immunotherapy
  作者：Jinmin Miao、Jiajun Dong、Yiming Miao、Yunpeng Bai、Zihan Qu、Brenson A. Jassim、Bo Huang、Quyen Nguyen、Yuan Ma、Allison A. Murray、Jinyue Li、Philip S. Low、Zhong-Yin Zhang

  DOI：10.1039/d3sc04541b

  日期：——

  We report the first, potent and selective PROTAC degrader for TC-PTP. The degrader enhances TC-PTP substrates’ phosphorylation levels, promotes antigen presentation in tumor, and enhances T-cell activation and CAR-T cell efficiency.

  我们报告了首个强效且具有选择性的 TC-PTP PROTAC 降解剂。这种降解剂能提高 TC-PTP 底物的磷酸化水平，促进肿瘤中的抗原呈递，并增强 T 细胞活化和 CAR-T 细胞的效率。
• Enantioselective synthesis of N-boc and N-fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine; agents suitable for the solid-phase synthesis of peptides containing nonhydrolyzable analogues of O-phosphotyrosine
  作者：Mark S. Smyth、Terrence R. Burke

  DOI：10.1016/s0040-4039(00)75835-7

  日期：1994.1

  Enantioselective convergent syntheses of N-Boc and N-Fmoc protected diethyl 4-phosphono(difluoromethyl)-L-phenylalanine are reported. le analogues of O-phosphotyrosine/
• Facile syntheses of aryldifluorophosphonate building blocks
  作者：G.Stuart Cockerill、Howard J. Easterfield、Jonathan M. Percy

  DOI：10.1016/s0040-4039(99)00266-x

  日期：1999.3

  The copper-catalysed zinc phosphonate chemistry described by Yokomatsu and Shibuya can be used directly in the synthesis of phosphotyrosine analogue F(2)Pmp, and in entering the classical organometallic coupling repertoire via Stille and Suzuki-Miyaura couplings. Herein, we report a streamlined synthesis of F(2)Pmp, and of a pivotal triflate, which undergoes a range of palladium-catalysed couplings with aryl and heteroaryl components. (C) 1999 Elsevier Science Ltd. All rights reserved.